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The crystal structure analysis of the title compound, C7H10O5, shows that a four-five lactonization instead of a four-six self condensation took place during the reaction sequence. The structure is stabilized by strong hydrogen-bonding interactions that serve to form a layer structure. The absolute configuration was assigned based on the chemical synthesis from a starting material of known chirality.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803014557/tk6117sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803014557/tk6117Isup2.hkl
Contains datablock I

CCDC reference: 221670

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.030
  • wR factor = 0.072
  • Data-to-parameter ratio = 8.7

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Yellow Alert Alert Level C:
STRVAL_01 From the CIF: _refine_ls_abs_structure_Flack -10.000 From the CIF: _refine_ls_abs_structure_Flack_su 10.000 Alert C Flack parameter is too small General Notes
REFLT_03 From the CIF: _diffrn_reflns_theta_max 28.30 From the CIF: _reflns_number_total 1107 Count of symmetry unique reflns 1105 Completeness (_total/calc) 100.18% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 2 Fraction of Friedel pairs measured 0.002 Are heavy atom types Z>Si present no Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF.
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
1 Alert Level C = Please check

Computing details top

Data collection: SMART-NT (Bruker, 1998); cell refinement: SAINT-Plus (Bruker, 1999); data reduction: SAINT-Plus and XPREP (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: DIAMOND (Brandenburg & Berndt, 2000); software used to prepare material for publication: SHELXL97.

(1R*,5S*,6S*,7R*)-6,7-Dihydroxy-6-hydroxymethyl-2-oxabicyclo[3.2.0]heptan-3-one top
Crystal data top
C7H10O5F(000) = 368
Mr = 174.15Dx = 1.543 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 698 reflections
a = 6.5888 (9) Åθ = 3.8–26.9°
b = 7.4342 (10) ŵ = 0.13 mm1
c = 15.303 (2) ÅT = 293 K
V = 749.59 (17) Å3Cuboid, colorless
Z = 40.46 × 0.26 × 0.18 mm
Data collection top
SMART CCD 1K area-detector
diffractometer
897 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.038
Graphite monochromatorθmax = 28.3°, θmin = 2.7°
ω scansh = 88
5322 measured reflectionsk = 89
1107 independent reflectionsl = 1820
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.030H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.072 w = 1/[σ2(Fo2) + (0.0441P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max < 0.001
1107 reflectionsΔρmax = 0.15 e Å3
127 parametersΔρmin = 0.16 e Å3
0 restraintsAbsolute structure: Flack (1983), 744 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 10 (10)
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O50.114852 (2)0.2488 (2)0.86512 (9)0.0403 (4)
O10.2810 (2)0.37971 (17)0.84311 (9)0.0370 (4)
O20.3558 (2)0.01718 (19)0.71149 (8)0.0332 (3)
O30.3195 (2)0.20206 (16)0.86719 (9)0.0370 (4)
O40.0636 (3)0.33747 (19)0.93400 (11)0.0529 (5)
C10.2408 (3)0.1914 (2)0.84292 (11)0.0254 (4)
C50.1534 (3)0.0307 (3)0.97439 (12)0.0339 (4)
H5A0.18860.04601.03550.041*
H5B0.01730.01850.97050.041*
C70.0270 (3)0.1583 (3)0.81039 (12)0.0288 (4)
H7A0.01390.20170.75090.035*
H7B0.00120.03020.81060.035*
C20.4075 (3)0.0876 (2)0.79413 (12)0.0263 (4)
C40.3054 (3)0.0914 (2)0.92869 (12)0.0301 (4)
C30.4357 (3)0.0373 (2)0.87276 (13)0.0309 (4)
C60.1678 (3)0.2052 (3)0.92644 (12)0.0338 (4)
H210.518 (4)0.161 (3)0.7918 (14)0.041*
H310.571 (3)0.070 (3)0.8904 (14)0.041*
H410.382 (3)0.161 (3)0.9698 (15)0.041*
H020.461 (4)0.014 (3)0.6925 (15)0.041*
H050.169 (4)0.339 (3)0.8313 (14)0.041*
H010.207 (4)0.429 (3)0.8692 (15)0.041*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O50.0326 (7)0.0473 (8)0.0410 (7)0.0118 (7)0.0053 (6)0.0020 (7)
O10.0380 (8)0.0200 (7)0.0530 (10)0.0014 (5)0.0132 (7)0.0043 (6)
O20.0296 (7)0.0371 (8)0.0328 (7)0.0002 (6)0.0044 (6)0.0087 (6)
O30.0465 (8)0.0236 (7)0.0407 (7)0.0021 (6)0.0143 (6)0.0000 (6)
O40.0695 (11)0.0344 (8)0.0549 (10)0.0126 (8)0.0225 (9)0.0022 (7)
C10.0281 (9)0.0198 (9)0.0284 (9)0.0029 (7)0.0035 (7)0.0001 (7)
C50.0433 (11)0.0319 (10)0.0266 (8)0.0031 (9)0.0060 (8)0.0007 (8)
C70.0296 (10)0.0289 (10)0.0281 (9)0.0038 (8)0.0018 (7)0.0010 (8)
C20.0221 (9)0.0235 (9)0.0333 (10)0.0025 (7)0.0020 (7)0.0023 (8)
C40.0333 (10)0.0301 (10)0.0268 (9)0.0023 (8)0.0052 (8)0.0043 (8)
C30.0261 (9)0.0289 (10)0.0378 (10)0.0040 (8)0.0001 (8)0.0029 (9)
C60.0421 (11)0.0288 (10)0.0306 (10)0.0026 (9)0.0056 (8)0.0049 (8)
Geometric parameters (Å, º) top
O5—C71.424 (2)C5—C61.493 (3)
O5—H050.92 (2)C5—C41.521 (3)
O1—C11.425 (2)C5—H5A0.9700
O1—H010.73 (2)C5—H5B0.9700
O2—C21.411 (2)C7—H7A0.9700
O2—H020.79 (3)C7—H7B0.9700
O3—C61.350 (2)C2—C31.531 (3)
O3—C31.447 (2)C2—H210.91 (2)
O4—C61.205 (2)C4—C31.544 (3)
C1—C71.514 (3)C4—H410.96 (2)
C1—C21.536 (2)C3—H310.97 (2)
C1—C41.568 (2)
C7—O5—H05105.7 (14)O2—C2—C3120.59 (16)
C1—O1—H01111.9 (17)O2—C2—C1116.71 (15)
C2—O2—H02103.0 (17)C3—C2—C190.56 (14)
C6—O3—C3111.52 (15)O2—C2—H21112.4 (14)
O1—C1—C7109.49 (15)C3—C2—H21107.4 (13)
O1—C1—C2111.21 (15)C1—C2—H21106.7 (14)
C7—C1—C2115.06 (14)C5—C4—C3104.55 (14)
O1—C1—C4114.46 (15)C5—C4—C1119.27 (16)
C7—C1—C4116.79 (15)C3—C4—C188.91 (14)
C2—C1—C488.52 (13)C5—C4—H41111.5 (13)
C6—C5—C4104.50 (15)C3—C4—H41113.9 (12)
C6—C5—H5A110.9C1—C4—H41116.0 (12)
C4—C5—H5A110.9O3—C3—C2113.75 (16)
C6—C5—H5B110.9O3—C3—C4105.24 (14)
C4—C5—H5B110.9C2—C3—C489.55 (13)
H5A—C5—H5B108.9O3—C3—H31107.0 (12)
O5—C7—C1109.87 (14)C2—C3—H31119.1 (13)
O5—C7—H7A109.7C4—C3—H31121.1 (13)
C1—C7—H7A109.7O4—C6—O3120.02 (17)
O5—C7—H7B109.7O4—C6—C5128.73 (17)
C1—C7—H7B109.7O3—C6—C5111.24 (17)
H7A—C7—H7B108.2
 

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